This study investigates novel and varied experiences of digital pilgrimage that are largely neglected in current pilgrimage studies. Digital pilgrimage is a viable method for partaking in the sacred ritual pilgrimage that is practised across various cultures as a form of journeying to and from places of sacred significance and as a form of ritualised obligation or meaning making. To date, the only discussions of digital based pilgrimages are Connie Hill- Smith’s article: Cyberpilgrimage: The (Virtual) Reality of Online Pilgrimage Experience (2011), and Mark MacWilliams two works: Virtual Pilgrimage to Ireland’s Croagh Patrick (2013), and Virtual pilgrimages on the internet (2002). All three come to similar conclusions about the disposition of digital based pilgrimages as being cyberspace-based environments. These studies assimilate both simple website-based pilgrimages with that of virtual reality. This can target a users’ exteroceptive senses (ocular, auditory, olfactory, and haptic), from three dimensional virtual environments to biometric feedback based on hand gestures in a virtual environment. These are dedicated not only for virtual reality (VR) pilgrimage, but also VR gaming and VR museum exhibitions. This thesis, therefore, proposes that digital pilgrimage needs to be considered more distinctly than it is currently, because the users’ interface and experience can be greatly affected by the various methods for interacting with the different digital environments of cyberspace, augmented reality, and virtual reality. It is also why the current study asserts the new concept of a “digital pilgrimage continuum” for examining a form of digital pilgrimage given there is an experiential and user interface difference between digitally mediated environments, including cyberspace, virtual reality, and augmented reality. The continuum involves a shift away from current definitions that maintain all digital based pilgrimages are the same. To support the need for this digital pilgrimage continuum this study also employs two other investigative strategies: 1) a comparative analysis of value based experience of digital pilgrimage drawing on insights from religious tourism to identify the experiential similarities between digital with non-digital pilgrimages, and 2) a theoretical perspective of viewing the virtuality debate in terms of notions of play drawing on insights from the game play theories of Dungeons and Dragons to differentiate between virtual as imagined and virtual reality as the computer generated environment for transformative experiences.